17064-77-6

Usage

Uses

Used in Chemical Synthesis:
N-(2-nitrobenzylidene)aniline is used as a precursor in the synthesis of various organic compounds, including azo dyes and pharmaceuticals, for its ability to undergo specific chemical reactions that facilitate the creation of these products.
Used as a pH Indicator:
In the field of chemistry and biology, N-(2-nitrobenzylidene)aniline serves as a pH indicator, leveraging its color-changing properties in response to different pH levels to measure and monitor acidity or alkalinity in solutions.
Used in Dye and Pigment Production:
N-(2-nitrobenzylidene)aniline is employed as a key component in the production of dyes and pigments, where its color characteristics are utilized to create a range of hues for various applications in industries such as textiles, paints, and plastics.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, N-(2-nitrobenzylidene)aniline is used in the synthesis of certain pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Safety Precautions:
When handling N-(2-nitrobenzylidene)aniline, it is crucial to adhere to proper safety measures due to its hazardous nature. This includes the use of personal protective equipment to prevent skin and eye contact, as well as implementing handling procedures that minimize exposure and potential health risks.

InChI:InChI=1/C13H10N2O2/c16-15(17)13-9-5-4-6-11(13)10-14-12-7-2-1-3-8-12/h1-10H/b14-10+

Upstream product

• 62-53-3 aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 612-25-9 2-Nitrobenzyl alcohol 
• 17064-86-7 N-(2-nitrobenzylidene)-4-nitroaniline 

Downstream Products

• 93-98-1 N-phenyl benzoyl amide 
• 142-04-1 aniline hydrochloride 
• 103582-31-6 3-(2-nitrophenyl)-2-carboxy-2-propenoic acid 
• 612-41-9 2-nitrocinnamic acid 
• 109772-87-4 2-(2-nitrophenyl)-2-phenylaminoacetonitrile 
• 20887-06-3 N-(2-aminobenzyl)aniline 
• 27126-08-5 2-nitroso-benzoic acid anilide 
• 52197-48-5 9b-methyl-4-(2-nitro-phenyl)-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 
• 98574-07-3 9b-methyl-4-(2-nitro-phenyl)-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 
• 3682-71-1 2-phenyl-2H-indazole 
• 10389-64-7 5-methyl-4-(2-nitro-benzylidene)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 102303-79-7 bis<4'-(3'-methyl-1'-phenylpyrazolin-5-one)yl>-2-nitrophenyl-methane 
• 33331-19-0 N-(2-nitrobenzyl)aniline 
• 117554-98-0 2-(2-Nitro-phenyl)-3H-1,3,8,9-tetraaza-anthracen-4-one 

Relevant academic research and scientific papers

Design, synthesis and anticandidal evaluation of indazole and pyrazole derivatives

Candidiasis, caused by yeasts of the genus Candida, is the second cause of superficial and mucosal infections and the fourth cause of bloodstream infections. Although some antifungal drugs to treat candidiasis are available, resistant strains to current therapies are emerging. Therefore, the search for new candicidal compounds is certainly a priority. In this regard, a series of indazole and pyrazole derivatives were designed in this work, employing bioisosteric replacement, homologa-tion, and molecular simplification as new anticandidal agents. Compounds were synthesized and evaluated against C. albicans, C. glabrata, and C. tropicalis strains. The series of 3-phenyl-1H-indazole moiety (10a–i) demonstrated to have the best broad anticandidal activity. Particularly, compound 10g, with N,N-diethylcarboxamide substituent, was the most active against C. albicans and both miconazole susceptible and resistant C. glabrata species. Therefore, the 3-phenyl-1H-indazole scaf-fold represents an opportunity for the development of new anticandidal agents with a new chemo-type.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Cysteine fluorescent probe and preparation method and application thereof

The invention discloses a cysteine fluorescent probe and a preparation method and application thereof. The cysteine fluorescent probe comprises quinolinium ions serving as a framework, trimethylsilyl bonded with the quinolinium ion skeleton structure through a carbon-silicon single bond, and a p-phenyl acrylate group and counter ions which are connected with the quinolinium ion skeleton structure through a carbon-carbon single bond. The fluorescence intensity of the cysteine fluorescent probe is almost completely quenched when cysteine is added, the fluorescence intensity of the cysteine fluorescent probe and the concentration of cysteine are correspondingly reduced according to a linear relation, and the cysteine fluorescent probe has high selectivity on cysteine, can distinguish cysteine from three biological mercaptans, and is suitable for being widely applied to detection of cysteine in living cells.

Synthesis and cytotoxic activity of combretastatin a-4 and 2,3-diphenyl-2h-indazole hybrids

Cancer is the second leading cause of death, after cardiovascular diseases. Different strategies have been developed to treat cancer; however, chemotherapy with cytotoxic agents is still the most widely used treatment approach. Nevertheless, drug resistance to available chemotherapeutic agents is still a serious problem, and the development of new active compounds remains a constant need. Taking advantage of the molecular hybridization approach, in the present work we designed, synthesized, and tested the cytotoxic activity of two hybrid compounds and seven derivatives based on the structure of combretastatin A-4 and 2,3-diphenyl-2H-indazole. Practical modifications of re-ported synthetic protocols for 2-pheny-2H-indazole and 2,3-dipheny-2H-indazole derivatives under microwave irradiation were implemented. The cytotoxicity assays showed that our designed hybrid compounds possess strong activity, especially compound 5, which resulted even better than the reference drug cisplatin against HeLa and SK-LU-1 cells (IC50 of 0.16 and 6.63 μM, respectively), and it had similar potency to the reference drug imatinib against K562 cells. Additionally, in silico and in vitro studies strongly suggest tubulin as the molecular target for hybrid compound 5.

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.

New yellow-emitting iridium(III) complexes containing 2-phenyl-2H-indazole-based ligands for high efficient OLEDs with EQE over 25%

Six new pidz-based bis-cyclometalated Ir(III) complexes (Ir1-Ir6) have been synthesized and characterized. These complexes contain 2-phenyl-2H-indazole (pidz, 2a), 2-(4-fluorophenyl)–2H-indazole (fpidz, 2b), 2-(p-tolyl)–2H-indazole (ch3pidz, 2c), 2-(4-(trifluoromethyl)phenyl)–2H-indazole (cf3pidz, 2d), 2-(2,4-difluorophenyl)–2H-indazole (2,4-f2pidz, 2e) and 2-(3,5-difluorophenyl)–2H-indazole (3,5-f2pidz, 2f) as cyclometalated (C∧N) ligands, and acetylacetone (acacH) as ancillary ligand. The crystal structure of Ir2 has been determined by X-ray analysis. Different substituents of C∧N ligand in Ir2-Ir6 induce either a bathochromic or hypsochromic shift in the absorption spectra relative to the parent complex Ir1. The phenomenon is further well explained by DFT calculation and electrochemical study. All of the iridium(III) complexes are yellow emissive with quantum yields of 13.1–32.3% and lifetimes of 1.32–1.77 μs in solution at room temperature. We demonstrate that their emission originates from a hybrid 3MLCT/3ILCT/3LLCT excited state on the basis of the experimental and theoretical investigation. The corresponding yellow-emitting devices based on complexes Ir1, Ir2 and Ir4 can produce efficient electrophosphorescence with a luminance efficiency of 35.1–52.2 cd·A-1, a power efficiency of 20.8–32.1 lm·W?1 and an external quantum efficiency of up to 25.6%. All these EL data definitely suggest the bulky –CF3 skeleton in the doped materials could benefit the fabrication of high-efficiency phosphorescent OLEDs.

Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media

Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]

Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides

A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.

Tunable Emission Color of Iridium(III) Complexes with Phenylpyrazole Derivatives as the Main Ligands for Organic Light-Emitting Diodes

Seven cyclometalated iridium(III) complexes Ir1-Ir7 based on phenylpyrazole derivatives as main ligands and tetraphenylimidodiphosphinate (tpip) as the ancillary ligand were synthesized and fully characterized. The proligands of 1-[4-(trifluoromethyl)phenyl]-1H-pyrazole (cf3ppz, 2a), substituted phenyl-2H-indazole {2-phenyl-2H-indazole (h-1-pidz, 2b), 2-(4-fluorophenyl)-2H-indazole (f-1-pidz, 2c), and 2-[4-(trifluoromethyl)phenyl]-2H-indazole (cf3-1-pidz, 2d)}, and substituted phenyl-1H-indazole {1-phenyl-1H-indazole (h-7-pidz, 2e), 1-(4-fluorophenyl)-1H-indazole (f-7-pidz, 2f), and 1-[4-(trifluoromethyl)phenyl]-1H-indazole (cf3-7-pidz, 2g)} were prepared with good yields. The emission maxima of all Ir(III) complexes can be tuned from 453 to 576 nm with different photoluminescence quantum yields (10.4-70.9%) by varying the type of substituent on the different main ligand frameworks. The organic light-emitting diodes using Ir(III) complexes as the emitters with blue, bluish-green, and yellow colors exhibit a maximum current efficiency and an external quantum efficiency of 39.2 cd A-1 and 14.8%, respectively.

Synthesis and biological evaluation of 2H-indazole derivatives: Towards antimicrobial and anti-inflammatory dual agents

Indazole is considered a very important scaffold in medicinal chemistry. It is commonly found in compounds with diverse biological activities, e.g., antimicrobial and anti-inflammatory agents. Considering that infectious diseases are associated to an inflammatory response, we designed a set of 2H-indazole derivatives by hybridization of cyclic systems commonly found in antimicrobial and anti-inflammatory compounds. The derivatives were synthesized and tested against selected intestinal and vaginal pathogens, including the protozoa Giardia intestinalis, Entamoeba histolytica, and Trichomonas vaginalis; the bacteria Escherichia coli and Salmonella enterica serovar Typhi; and the yeasts Candida albicans and Candida glabrata. Biological evaluations revealed that synthesized compounds have antiprotozoal activity and, in most cases, are more potent than the reference drug metronidazole, e.g., compound 18 is 12.8 times more active than metronidazole against G. intestinalis. Furthermore, two 2, 3-diphenyl-2H-indazole derivatives (18 and 23) showed in vitro growth inhibition against Candida albicans and Candida glabrata. In addition to their antimicrobial activity, the anti-inflammatory potential for selected compounds was evaluated in silico and in vitro against human cyclooxygenase-2 (COX-2). The results showed that compounds 18, 21, 23, and 26 display in vitro inhibitory activity against COX-2, whereas docking calculations suggest a similar binding mode as compared to rofecoxib, the crystallographic reference.